The microreview surveys the methods of synthesis of thieno[2,3-b]indoles described in the literature, the most important of which are the thiophene ring annulation to indole, closure of the pyrrole ring in 3-arylthiophenes, as well as cyclization reactions of aryl isothiocyanates.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Soledade, M.; Pedras, C.; Suchy, M. Bioorg. Med. Chem. 2006, 14, 714.
An-naka, M.; Yasuda, K.; Yamada, M.; Kawai, A.; Takamura, N.; Sugasawa, S.; Matsuoka, Y.; Iwata, H.; Fukushima, T. Heterocycles 1994, 39, 251.
Kobayashi, G.; Matsuda, Y.; Tominaga, Y.; Ohkuma, M.; Shinoda, H.; Kohno, M.; Mizuno, D. Yakugaku Zasshi 1977, 97, 1033.
Gurova, K.; Rydkina, E. B.; Wade, W. WO Patent 2015050472A1.
Karmatsky, A. A.; Charushin, V. N.; Irgashev, R. A.; Rusinov, G. L. RU Patent 2565072.
Baert, F.; Cabanetos, C.; Allain, M.; Silvestre, V.; Leriche, P.; Blanchard, P. Org. Lett. 2016, 18, 1582.
Irgashev, R. A.; Karmatsky, A. A.; Kozyukhin, S. A.; Ivanov, V. K.; Sadovnikov, A.; Kozik, V. V.; Grinberg, V. A.;Emets, V. V.; Rusinov, G. L.; Charushin, V. N. Synth. Met. 2015, 199, 152.
Kanbe, K.; Naganawa, H.; Nakamura, K. T.; Okami, Y.; Takeuchi, T. Biosci., Biotechnol., Biochem. 1993, 57, 636.
Boeini, H. Z. Helv. Chim. Acta 2009, 92, 1268.
Savych, I.; Gläsel, T.; Villinger, A.; Sosnovskikh, V. Ya.; Iaroshenko, V. O.; Langer, P. Org. Biomol. Chem. 2015, 13, 729.
Moghaddam, F. M.; Saeidian, H.; Mirjafary, Z.; Taheri, S.; Kheirjou, S. Synlett 2009, 1047.
Velezheva, V. S.; Lepyoshkin, A. Yu.; Turchin, K. F.; Fedorova, I. N.; Peregudov, A. S.; Brennan, P. J. J. Heterocycl. Chem. 2013, 50, 225.
Majumdar, K. C.; Alam, S. J. Chem. Res. 2006, 289.
Liao, Y.; Peng, Y.; Qi, H.; Deng, G.-J.; Gong, H.; Li, C.-J. Chem. Commun. 2015, 51, 1031.
Kobayashi, G.; Furukawa, S.; Matsuda, Y.; Natsuki, R. Yakugaku Zasshi 1969, 89, 58.
Levy, J.; Royer, D.; Guilhem, J.; Cesario, M.; Pascard, C. Bull. Soc. Chim. Fr. 1987, 193.
Irgashev, R. A.; Karmatsky, A. A.; Rusinov, G. L.; Charushin, V. N. Beilstein J. Org. Chem. 2015, 11, 1000.
Singh, P. P.; Yadav, A. K.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2011, 4001.
Yadav, A. K.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2010, 338.
Acharya, A.; Kumar, S. V.; Saraiah, B.; Ila, H. J. Org. Chem. 2015, 2884.
Acharya, A.; Kumar, S. V.; Ila, H. Chem.–Eur. J. 2015, 21, 17116.
Aurelio, L.; Volpe, R.; Halim, R.; Scammells, P. J.; Flynn, B. L. Adv. Synth. Catal. 2014, 356, 1974.
Olesen, P. H.; Hansen, J. B.; Engelstoft, M. J. Heterocycl. Chem. 1995, 32, 1641
Engqvist, R.; Javaid, A.; Bergman, J. Eur. J. Org. Chem. 2004, 2589.
Appukkuttan, P.; Van der Eycken, E.; Dehaen, W. Synlett 2005, 127.
Smitrovich, J. H.; Davies, I. W. Org. Lett. 2004, 6, 533.
Gao, H.; Xu, Q.-L.; Yousufuddin, M.; Ess, D. H.; Kürti, L. Angew. Chem., Int. Ed. 2014, 53, 2701.
Kienle, M.; Wagner, A. J.; Dunst, C.; Knochel, P. Chem. Asian. J. 2011, 6, 517.
Saito, T.; Nihei, H.; Otani, T.; Suyama, T.; Furukawa, N.; Saito, M. Chem. Commun. 2008, 172.
Otani, T.; Kunimatsu, S.; Takahashi, T.; Nihei, H.; Saito, T. Tetrahedron Lett. 2009, 50, 3853.
Butin, A. V.; Tsiunchik, F. A.; Abaev, V. T.; Zavodnik, V. E. Synlett 2008, 1145.
Butin, A. V.; Tsiunchik, F. A.; Abaev, V. T. RU Patent 2345082 C1.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(10), 779–781
Rights and permissions
About this article
Cite this article
Egorov, D.I. Synthesis of thieno[2,3-b]indoles (microreview). Chem Heterocycl Comp 52, 779–781 (2016). https://doi.org/10.1007/s10593-016-1964-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-016-1964-x